


I Love A Challenge

by imtorimountain



Category: IT (2017), IT - Stephen King
Genre: Aged-Up Character(s), Alternate Universe - Modern Setting, Bartender AU, Bartender Eddie, M/M, they're 23 ish
Language: English
Status: Completed
Published: 2018-06-14
Updated: 2018-06-14
Packaged: 2019-05-23 08:29:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,920
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14930756
Author URL: https://archiveofourown.org/users/imtorimountain/pseuds/imtorimountain
Summary: Hi babes! I know, I know, I should be working on chapter 4 of In Another Life, but I found this fanfic hidden in my writing folder last night. It originally had a second part, and it was originally about two YouTubers. Meaning that this fanfic is three years old...It was interesting to revisit my old writing and see how I've developed. Not much, I noticed. But despite this being about real life people, I actually liked the story. The best part was that if I changed the names, it was really in character for Richie and Eddie.So, I just switched out all the names and updated the dialogue, and now it's a Reddie fic! I hope you like it ❤





	I Love A Challenge

**Author's Note:**

> Hi babes! I know, I know, I should be working on chapter 4 of In Another Life, but I found this fanfic hidden in my writing folder last night. It originally had a second part, and it was originally about two YouTubers. Meaning that this fanfic is three years old...  
> It was interesting to revisit my old writing and see how I've developed. Not much, I noticed. But despite this being about real life people, I actually liked the story. The best part was that if I changed the names, it was really in character for Richie and Eddie.  
> So, I just switched out all the names and updated the dialogue, and now it's a Reddie fic! I hope you like it ❤

With his phone in his hand and his leather jacket hanging over his arm, Richie pushed through the crowd, his head held high. The music in the club was loud enough to make his ears numb, but he didn’t mind. As soon as he managed to make his way over to where his friends were sitting, he would be out on the dance floor and having fun. He just had to put his stuff down first.

He made his way to the bar and sat down at the chair Beverly had managed to save for him. He leaned over and kissed her on the cheek, their usual greeting of seven years.

“How are you, my darling Beverly?” he yelled over the music as he waved for the bartender. He hung his jacket over the back of his chair.

“I’m just fine, Richie,” Beverly replied and sipped her drink. She nodded at the occupied seats next to her. “Bill and Stan couldn’t make it. They had to babysit Georgie.”

“Parents out of town again?” Richie wondered. He turned to the bartender – the really fucking _cute_ bartender – and ordered a drink as Beverly nodded.

“Yeah,” she said. She had some more of her drink and put it down on the table. “So I’m glad that your date was cancelled.”

Her eyes widened, and she was probably blushing although Richie couldn’t tell because of the dark lighting. “Wait,” she stammered. “I-I didn’t mean it like that, Rich, I’m just glad you could make it so I wouldn’t be alone-”

Richie silenced her with his laugh. “It’s cool, Bev, I get it.” He put his phone in his pocket and pulled Beverly’s drink toward him. “I’m glad too; it didn’t seem like I would’ve been able to go on more than one date anyway when she texted me that she might be late since she was, ah, how do I put this…” He took a sip of Beverly’s drink and made a face. “Shit Bev, I’ve told you, calm down with the fucking rum.” Beverly laughed as he wiped his mouth on his hand.

“I’ll put it like this,” Richie continued, “she didn’t seem _reliable_ when she texted me that she might be late since she was at her boyfriend’s house.”

Beverly, who had just reached for her drink again, burst out laughing and almost knocked her glass to the floor. Richie just grinned and watched his friend bend over with laughter. Beverly stayed still for nearly five seconds before she straightened back up again and fanned her face in an attempt to get some air.

“I’m sorry Richie,” she said while gasping for air, “but that was the best one since that guy who ran the other direction when he saw you at the restaurant because he thought your profile picture was of a girl.”

Richie laughed and shook his head. “Just my dumbass luck in dating, huh? I know I’ve said that I love a challenge, but this shit’s getting a little too challenging.”

The cute bartender arrived with Richie’s drink and Beverly held up her own. “Here’s to two losers who can’t seem to find their significant other.”

Richie lifted his glass and clinked it with Beverly’s. “Bev, for one, what you’ve got going on with Haystack seems a lot like a significant other thing to me. And second, you know the only significant other I need is my best friend. And she’s sitting right in front of me.”

Beverly kicked Richie in the shin. “Sentimentality doesn’t suit you, Tozier. Just shut up and try your fucking drink.”

Richie laughed. They both drank from their glasses and put them down at the same time.

“So how long until you leave me for the dance floor?” Beverly asked as she beckoned for the bartender. Richie shrugged and stirred his drink with his finger. “When I’ve finished this probably. Since Billiam and Staniel aren’t here I might have a second one though, just to keep you company. Hey, hold the rum,” he added to the bartender, who grinned and put the rum bottle back on the shelf behind him.

Something stirred in Richie’s mind when he saw the smile. He had seen that smile somewhere before.

Beverly’s scoff brought him back. “You know this is _my_ drink, right?” his friend teased and flicked a few drops at Richie’s face. “I can have whatever the hell I want in it.”

“Beverly, my love, you haven’t seen yourself when you’re drunk on rum,” Richie said with a chuckle and wiped the alcohol from his cheek. “It’s the most beautifully terrifying thing in the world. God, I wish I had filmed when you ran over your neighbours’ garden…”

“Pervert,” Beverly said and sipped her drink. “I was eighteen and naked.”

“And I was nineteen and almost naked,” Richie replied. “Sure, it may have been four years ago, but dear God, I still wish I had filmed it. Best thing I’ve seen in my life.”

“Poor squirrel,” Beverly mumbled into her drink, then broke into a fit of giggles. “Oh God, the fucking squirrel.”

“And the giggling begins,” Richie noted. “The first sign of a little too much rum in Beverly Marsh’s body.” He removed the little umbrella from his glass and stuck it behind Beverly’s ear. “The second sign, getting emotional over teeny tiny gifts, will likely begin in three, two, one…”

Beverly slapped his hand away and removed the umbrella from her ear. She dropped it on the table and flipped Richie off while taking another sip of her drink. Richie just waited. Any second now.

“It _is_ a cute umbrella,” Beverly admitted as she put her glass down. “I wish I could have one of them every day. Aw man, I want one in my hair every day…”

Richie snorted and Beverly realized what she was doing. She tore her eyes from the umbrella and threw it at Richie. “Fuck off! You’ve known me since I was sixteen, it’s not fair!”

Richie threw the umbrella back at her. “But I’ve only seen the glorious effects of you combined with rum for five years.”

“Still,” Beverly grumbled and put the umbrella behind her ear again. She drank again and looked at Richie.

“So, when are you going to tell me why you ditched the person you were going to see the other day?” she wondered and leaned her head in her left hand. “You know, that charming guy who also turned out to be from Derry.”

“He was the one who cancelled, Bev,” Richie said and downed the rest of his drink. He waved at the bartender. “He texted me and told me he had gotten a cold.”

“What was his name again?” Beverly asked. “Eric?”

“Eddie,” Richie corrected her. “Eddie Kaspbrak, I think.”

A crash was heard, and less than a second later Beverly yelped and jumped out of her seat.

“Oh my God, I’m so sorry!” the bartender exclaimed. He had dropped Richie’s glass as he was refilling it and the contents had spilled right onto Beverly. The front of her top was soaked in vodka and she carefully shook it to get rid of the glass shards that were stuck in the fabric.

“Bev, are you okay?” Richie got up from his chair and bent down to pick the bigger glass pieces from the floor. He put them on the table and turned to the bartender who was frantically wiping up the alcohol with a towel. “Excuse me, do you have an extra towel?” Richie asked. “There’s some on the floor as well.”

“Ah, no, I’ve got it,” the bartender said. “You don’t have to do anything.”

“Oh please,” Richie said and held his hand out. “Towel.”

The bartender hesitated for a moment before he smiled gratefully at Richie. He reached down to a cupboard beneath the bar and brought out a clean towel that he handed to him.

“Thank you,” he said. Richie shrugged. “No problem, dude.” He smiled back at the bartender and then bent down to mop up the alcohol at his feet.

When he stood back up he put the towel on the bar and turned to his friend. “You okay, Bev?”

Beverly nodded. “Yeah, I’m okay. I just wasn’t ready.” She turned to the bartender. “Could you point me in the direction of the ladies’ room?”

The bartender gestured towards a door near the back of the club. Bev briefly bumped her fist with Richie’s and promised to be back within ten minutes, then she left.

Richie sat down again and turned to the bartender. “You good?”

The bartender nodded. “Yeah, I’m alright.” He wiped away the last drops of vodka from the bar surface and tossed both his towel and the one Richie had used in a drawer next to him. He looked up at Richie and smiled awkwardly at him. “Thanks again for helping me.”

“It was nothing,” Richie waved him off.

The bartender reached for another glass and the bottle of vodka that was still standing next to him. “Still want that drink? It’s on the house.”

“You flirting with me or something?” Richie questioned with a wink. The bartender grinned and started making Richie’s drink again. “I’m taking that as a yes,” he laughed and flipped his hair out of his face with the bottle. As he added an umbrella, Richie’s phone beeped. He brought it out and read the text from Beverly.

**_Beverly Marsh – received @ 9:29 PM_ **

_Ran into Ben outside the bathroom. He’s heading back home now & asked if I wanted to come with him. You cool with that? _

Richie typed his reply with a grin on his face.

**_Richie Tozier – sent @ 9:30 PM_ **

_Knock urself out, babe_

**_Richie Tozier – sent @ 9:30 PM_ **

_But hold the rum. & use protection ;) _

Beverly’s reply came immediately.

**_Beverly Marsh – received @ 9:30. PM_ **

_1, beep beep. 2. Only if you promise to get the bartender’s number_

**_Beverly Marsh – received @ 9:31 PM_ **

_He was totally checking your ass as you were cleaning the floor_

Richie put his phone in his pocket again and directed his attention back to the bartender who slid the drink across the bar to Richie. Richie picked it up and raised the glass to the bartender. “Join me?”

“Who’s the one flirting now?” the bartender chuckled. “I’m afraid I’m not allowed to drink on the job.” He looked up at the clock behind him. “But my shift ends in half an hour if you're willing to wait?”

“Would you be upset if I said I’m not?”

The bartender smirked. “You wouldn’t know what you were missing.” He filled a glass with water and raised it to Richie’s glass. They met with a low clinking sound. “But if you really don’t want to stay, I’ll hold the door for you as you leave.”

“Are you just teasing or are you playing hard to get?” Richie wondered with a slight tilt of the head. “I’m usually good at seeing the difference but something with you is… I don't know.”

“Off?” the bartender suggested. “Weird? Not right?”

“Different,” Richie decided. He smiled and finally lowered his glass, which he had been holding against the bartender’s ever since the glasses clinked.

He raised the glass to his lips and drank half of the drink at once. He looked back at the bartender as he put his glass down. Once again he recognized the man’s smile. He had definitely seen him somewhere before.

As soon as the thought crossed Richie’s mind, his eyes widened and he nearly dropped the glass himself.

“Eddie Kaspbrak?”

The bartender’s smile vanished. He straightened up and emptied his water glass in the sink next to him. He turned back to Richie, his previous flirty self gone. “Hi, Richie.”

Richie put his glass down and leaned against the bar. “That’s why you dropped my glass earlier!” he said with a grin. “You heard me mention you! Man, I didn’t know you worked here.”

Eddie smiled sheepishly and fumbled with his glass. “Yeah, well… Hi.”

Richie leaned his hand in his hand. “You’re way more attractive in real life than in your dating profile.”

Eddie laughed slightly. “Is that a compliment or are you saying that I should change my profile picture?”

Richie shrugged. “Until we’ve made up for that date we missed on Tuesday, I don’t really mind what you do with your profile picture,” he said with a wink.

Eddie’s smile widened. “I didn’t think you’d want to go on a date after I cancelled an hour before we were supposed to meet.”

“You were sick, of course you had to cancel,” Richie said and waved his hand. “It’s totally fine. But do you _want_ to go on a date with me?”

Eddie laughed. “That’s incredibly straightforward, you know.”

“Eds, my man, nothing I do is straight,” Richie said and winked.

Eddie wrinkled his nose, successfully making Richie’s heart do somersaults as a reaction. “Ugh, where did Eds come from?”

“Somewhere,” Richie said and shrugged. “Nowhere special. Why?”

“I’m not so sure I like it,” Eddie replied.

“Are you playing hard to get or just teasing again?” Richie said with another wink. He removed the umbrella from his drink and dragged his finger in circles along the edge of the glass. Eddie watched his hand for a split second before he looked back at Richie.

“No, I genuinely don’t really like that nickname,” he answered and put his empty glass down. “And also, I’m just saying that now that we’ve met for real, you could at least ask me out properly.”

Richie smirked. “Eds, Eddie, or Edward Kaspbrak,” he started. “Would you like to go on a date with me, a humble nobody who would be beyond honored if you accepted this offer?”

Eddie rolled his eyes and smiled, but before he could answer, a woman sitting at the other end of the bar snapped her fingers. “Bartender!”

Eddie clenched his teeth together. “Let me guess. She’s got long blonde hair in a ponytail.”

Richie looked over at the woman and nodded. “Yup. Big hoop earrings and a ridiculously low cut dress.”

Eddie cursed and closed his eyes. “She comes here every Friday night. I think she’s gotten into her head that I’m straight.”

“Bartender!!” the woman hollered again.

“Shift ends at ten,” Eddie said and smiled slightly at Richie. “See you outside five past?”

Richie nodded. “See you.”

Eddie turned and walked over to the blonde woman and started talking to her. Richie’s eyes wandered down to briefly linger on Eddie’s ass as he finished his drink and brought his phone out. He started typing up a text to Beverly.

**_Richie Tozier – sent @ 9:34 PM_ **

_He’s Eddie fucking Kaspbrak_

Beverly’s reply didn’t come for a while, so Richie scrolled through Instagram and Twitter for a while. When his phone buzzed at 9:49, he wasn’t surprised at Beverly’s response.

**_Beverly Marsh – received @ 9:49 PM_ **

_RICHIE MOTHERFUCKING TOZIER TELL ME YOU’RE JOKING_

**_Beverly Marsh – received @ 9:49 PM_ **

_RICHIE OH MY GOOOD_

**_Beverly Marsh – received @ 9:50 PM_ **

_Richard Tozier, if you don’t hook the fuck up with that man I am going to tell EVERYONE that you met a cute boy who was flirting with you and you didn’t flirt back_

Richie laughed and played with the umbrella from his drink with his left hand as he typed with his right.

**_Richie Tozier – sent @ 9:51 PM_ **

_Then u would be lying, Bev. I DID flirt back_

**_Richie Tozier – sent @ 9:51 PM_ **

_ & not a little, either _

**_Richie Tozier – sent @ 9:51 PM_ **

_His butt is gr8, 10/10 would smash_

Richie could almost hear Beverly’s excited chattering as “ _Read @ 9:51 PM_ ” popped up beneath his text. He glanced backwards to where Eddie was still talking to the blonde woman, a pained expression on his face.

His phone buzzed again and he turned his focus back to Beverly’s texts.

**_Beverly Marsh – received @ 9:52 PM_ **

_Hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up hook up_

**_Beverly Marsh – received @ 9:52 PM_ **

_Pleeeaaase_

**_Beverly Marsh – received @ 9:54 PM_ **

_Hey Richie, I took Bev’s phone. On behalf of all of our friends; go on a date and fall in love with that guy._

**_Beverly Marsh – received @ 9:54 PM_ **

_Thanks! /Ben_

**_Beverly Marsh – sent @ 9:55 PM_ **

_I’m gonna murder Ben_

**_Beverly Marsh – received @ 9:55 PM_ **

_He held me back with ONE HAND as he was texting_

While Bev and Ben had been texting Richie, he had taken his jacket that was still hanging on his chair and gotten up to walk outside. He leaned against the wall next to the entrance to the club and smiled at his phone.

He glanced at the clock at the top of the screen. Ten minutes until Eddie was supposed to come outside and meet him.

His phone started vibrating and showed that Beverly was calling him. He answered and held the phone up to his ear.

“ _Haystack, give Bev her phone back_ ,” he said with a laugh. Beverly’s voice replied, from a distance, “ _yeah, Ben!!_ ”

“ _But Rich!_ ” Ben complained, “ _this is such an great thing! You just met the guy who you were swooning about for like, what, a week?_ ”

“Wow, Haystack, stalker much?” Richie said and laughed. “Yeah, I met him. His shift ends in four minutes, and we decided to get a drink. Not here though; he said to meet him outside five past ten.”

“ _That is disgusting but cute_ ,” a third voice chimed in.

“Ayy, Mikey!” Richie said and laughed. He reached into the pocket of his jacket and brought out a pack of cigarettes. “When’d you show up, Homeschool?”

“ _I just got on the train_ ,” Mike explained. “ _Happened to see these two lovebirds and they quickly filled me in on what’s going on with you_.”

“ _Anyway, I wish you the best of luck_ ,” Beverly mock cooed. “ _When are you meeting him?_ ”

“In about ten minutes.”

“ _Alright, good luck!_ ” Beverly said. “ _I need all the details tomorrow, Tozier_.”

“You got it, babe,” Richie answered. “Bye Haystack, see ya Mikey.”

The other guys said goodbye and then they hung up. Richie slipped his phone back in his pocket and fished a lighter out of his jacket after putting a cigarette between his lips.

He lit the cigarette and leaned his head back against the wall. Far up, between the rooftops of New York, he could see the night sky. The many streetlights and the polluted air, as well as the smoke from his cigarette, blocked the view of the stars, but he could see the bright crescent shape of the moon. It shone with a bright light upon the never resting city.

Richie closed his eyes and stayed leaned against the wall for a few more minutes, taking slow drags of his cigarette and listening to the sounds of New York.

“You look great when you’re standing like that,” Eddie’s voice suddenly said to his right. Richie’s eyes snapped open and he turned to look at him. He smiled widely and pushed himself away from the wall.

“Thanks,” he said and looked Eddie up and down. Now that he wasn’t behind a bar, Richie could see all of him. He was shorter than Richie had expected. His wavy brown hair framed his face nicely, and he was wearing a white and pink sweater tucked into light blue jeans. He had a backpack slung over his shoulder.

“Did you get away from Blondie?” Richie asked and dropped the butt of his cigarette to the ground as he started putting on his jacket.

“Myra,” Eddie replied and nodded. “Yeah, but only barely.” He put his hands in the pockets of his jeans. He looked at Richie and beckoned with his head towards the street. “You ready to get out of here?”

“I’d love to,” Richie replied with a grin. “Where do you plan on taking me?”

Eddie started walking and Richie followed. “I was going to ask if you’d like to take a walk or come over to my place and have a drink.” He kicked an empty beer can on the road and sent it twenty feet ahead of the two men. “The second option may seem a little rushed, but as you’ve noticed, I know how to mix,” he added with a laugh.

Richie laughed as well and kicked the same beer can that Eddie had previously kicked. It landed with a clatter thirty feet ahead. “I’d like that.”

“Then it’s settled,” Eddie smiled. He flipped his head to get his hair out of his face.

A cold breeze swept through the street. It ruffled the leaves in the bushes and trees and messed up the mens’ hair. Eddie shivered and pressed his arms close to his body. Richie noticed and a worried expression crossed his face. “Hey man, you okay?”

“Yeah,” Eddie nodded. “I’ll be fine.”

Richie thought for a second and then started taking his jacket off. “Here,” he said and handed the jacket to Eddie.

Eddie looked at it and then at Richie. “What? No, it’s yours! You'll be cold if you don't have it.”

“Put on the jacket, Eds.” Richie stopped walking and grabbed Eddie’s arm to pull him to halt. “Come on.”

Eddie hesitated for a moment before he smiled and took the jacket. “Thank you,” he said as he pulled the jacket on. He placed his hands in the pockets and sighed. “That’s really warm.” He looked back at Richie. “Don’t call me Eds though.”

“How about Eddie Spaghetti?” Richie asked with a grin and put his own hands in the pockets of his jeans.

“That’s definitely worse,” Eddie said and rolled his eyes.

Richie laughed. “If you want to go on a date with me you’ll have to get used to it, dude.”

“Then maybe I don’t want to go on a date with you, Tozier,” Eddie shot back.

Richie placed a hand over his chest and gasped. “That is so rude, Eds. I trusted you.”

“Worst decision of your life,” Eddie said with a shrug.

Richie grinned and let his hand drop. He started walking again, but Eddie grabbed his arm and pulled him back. The sudden movement made Richie stumble slightly and he ended up really close to Eddie, their breaths mixing in the cool November air.

Richie looked into Eddie’s eyes, and he felt his breath catch in his throat. Several shades of brown, from the darkest coffee imaginable to the gentle hue of milk chocolate. Strands of hazelnut and hot cocoa and heavy oak doors provided more depth and life.

For the first time since they met half an hour ago, Richie really _looked_ at Eddie. Not just his eyes, but the rest of his face too. He could tell that Eddie was doing the same.

Richie studied Eddie’s face for what felt like forever, and for a moment, he was lost in the other man’s gaze.

Eddie clearing his throat made Richie blink, and just like that, the moment was gone. He took a small step away from Eddie and looked down at their feet.

“You were going the wrong way,” Eddie said quietly, his hand still on Richie’s arm. “My, um, my apartment’s the other way.”

Richie nodded and looked up, back at Eddie. “Right.” He took a deep breath and grinned. “Let’s go then.”

Eddie smiled back. “Yeah.”

**Author's Note:**

> Thank you for reading!! Don't be afraid to leave kudos and maybe a comment ❤


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